3-(heterocyclyl)-substituted benzolpyrazols

ABSTRACT

The invention relates to 3-(heterocyclyl)-substituted benzoylpyrazois of formula (I), wherein the variables have the following meanings: X is O, NH or N-alkyl; R 1  is alkyl; R 2 , R 3 , R 4 , R 5  are hydrogen, alkyl or alkyl halide; R 6  is halogen, nitro, alkyl halide, alkoxy, halogenalkoxy, alkylthio, halogenalkylthio, alkylsulfonyl or halogenalkylsulfonyl; R 7  is hydroxy, alkoxy, alkenyloxy, alkylsulfonyloxy, alkylcarboyloxy, alkylthiocarbonyloxy, phenylsulfonyloxy or phenylcarbonyloxy, and the phenyl radical can be substituted; R 8 , R 9  are alkyl; R 10  is hydrogen or alkyl; and R 11  is hydrogen or alkyl; and to their agriculturally useable salts. The invention also relates to intermediate products and methods for producing the inventive compounds and to the use of these compounds or products containing them for combating undesirable plants.

The present invention relates to 3-(heterocyclyl)-substitutedbenzoylpyrazoles of the formula I

where:

X is O, NH or N(C₁-C₆-alkyl);

R¹ is C₁-C₆-alkyl;

R², R³, R⁴, R⁵ are hydrogen, C₁-C₄-alkyl or C₁-C₄-haloalkyl;

R⁶ is halogen, nitro, C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy,C_(l)-C₄-alkylthio, C₁-C₄-haloalkylthio, C₁-C₄-alkylsulfonyl orC₁-C₄-haloalkylsulfonyl;

R⁷ is hydroxyl, C₁-C₆-alkoxy, C₃-C₆-alkenyloxy, C₁-C₆-alkylsulfonyloxy,C₁-C6-alkylcarbonyloxy, C₁-C₄-(alkylthio)carbonyloxy, phenylsulfonyloxyor phenylcarbonyloxy, where the phenyl radical of the two last-mentionedsubstituents may be partially or fully halogenated and/or may carry oneto three of the following groups:

nitro, cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy orC₁-C₄-haloalkoxy;

R⁸, R⁹ are C₁-C₄-alkyl;

R¹⁰ is hydrogen or C₁-C₄-alkyl;

where the number of the carbon atoms of the radicals R⁸, R⁹ and R¹⁰together is at most 7,

R¹¹ is hydrogen or C_(l)-C₄-alkyl;

and their agriculturally useful salts.

Moreover, the invention relates to intermediates and processes forpreparing compounds of the formula I, to compositions comprising themand to the use of these derivatives or of compositions comprising themfor controlling harmful plants.

Pyrazol-4-yl benzoyl derivatives are disclosed in the literature, forexample in WO 96/26206 and WO 98/31681.

However, the herbicidal properties of the prior-art compounds and theircompatibility with crop plants are not entirely satisfactory.

It is an object of the present invention to provide novel, in particularherbicidally active, compounds having improved properties.

We have found that this object is achieved by the3-(heterocyclyl)-substituted benzoylpyrazoles of the formula I and theirherbicidal action.

Furthermore, we have found herbicidal compositions which comprise thecompounds I and have very good herbicidal action. Moreover, we havefound processes for preparing these compositions and methods forcontrolling undesirable vegetation using the compounds I.

Depending on the substitution pattern, the compounds of the formula Imay contain one or more chiral centers, in which case they are presentas enantiomers or mixtures of diastereomers. The invention provides boththe pure enantiomers or diastereomers and their mixtures.

The compounds of the formula I can also be present in the form of theiragriculturally useful salts, the kind of salt usually being immaterial.In general, the salts of those cations or the acid addition salts ofthose acids are suitable whose cations and anions, respectively, do notadversely affect the herbicidal action of the compounds I.

Suitable cations are, in particular, ions of the alkali metals,preferably lithium, sodium and potassium, of the alkaline earth metals,preferably calcium and magnesium, and of the transition metals,preferably manganese, copper, zinc and iron, and also ammonium, where,if desired, one to four hydrogen atoms may be replaced by C₁-C₄-alkyl,hydroxy-C₁-C₄-alkyl, C₁-C₄-alkoxy-C₁ -C₄-alkyl,hydroxy-C₁-C₄-alkoxy-C₁-C₄-alkyl, phenyl or benzyl, preferably ammonium,dimethylammonium, diisopropylammonium, tetramethylammonium,tetrabutylammonium, 2-(2-hydroxyeth-1-oxy)eth-1-ylammonium,di(2-hydroxyeth-1-yl)ammonium, trimethylbenzylammonium, furthermorephosphonium ions, sulfonium ions, preferably tri(C₁-C₄-alkyl)sulfonium,and sulfoxonium ions, preferably tri(C₁-C₄-alkyl)sulfoxonium.

Anions of useful acid addition salts are primarily chloride, bromide,fluoride, hydrogen sulfate, sulfate, dihydrogen phosphate, hydrogenphosphate, nitrate, bicarbonate, carbonate, hexafluorosilicate,hexafluorophosphate, benzoate and the anions of C₁-C₄-alkanoic acids,preferably formate, acetate, propionate and butyrate.

The organic molecular moieties mentioned for the substituents R¹ -R¹¹ oras radicals on phenyl rings are collective terms for individualenumerations of the individual group members. All hydrocarbon chains,i.e. all alkyl, alkylcarbonyl, haloalkyl, alkoxy, haloalkoxy,alkylcarbonyloxy, (alkylthio)carbonyloxy, alkylsulfonyloxy, alkylthio,haloalkylthio, alkylsulfonyl, haloalkylsulfonyl, alkenyl and alkenyloxymoieties can be straight-chain or branched. Unless indicated otherwise,halogenated substituents preferably carry one to five identical ordifferent halogen atoms. The term “halogen” represents in each casefluorine, chlorine, bromine or iodine.

Examples of other meanings are:

C₁-C₄-alkyl, and the alkyl moieties of C₁-C₄-alkylcarbonyl andC₁-C₄-alkylcarbonyloxy: for example methyl, ethyl, propyl,1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl and1,1-dimethylethyl;

C₁-C₆-alkyl, and the alkyl moieties of C₁-C₆-alkylcarbonyl andC₁-C₆-alkylcarbonyloxy: C₁-C₄-alkyl as mentioned above, and also, forexample, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl,2,2-dimethylpropyl, 1-ethylpropyl, hexyl, 1,1-dimethylpropyl,1,2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl,4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl,2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl,2-ethylbutyl, 1,1,2-trimethylpropyl, 1-ethyl-1-methylpropyl and1-ethyl-3-methylpropyl;

C₁-C₄-haloalkyl: a C₁-C₄-alkyl radical as mentioned above which ispartially or fully substituted by fluorine, chlorine, bromine and/oriodine, i.e., for example, chloromethyl, dichloromethyl,trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl,chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl,bromomethyl, iodomethyl, 1-fluoroethyl, 1-chloroethyl, 1-bromoethyl,1-iodoethyl, 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2-iodethyl,2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl,2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl,2,2,2-trichloroethyl, pentafluoroethyl, 2-fluoropropyl, 3-fluoropropyl,2,2-difluoropropyl, 2,3-difluoropropyl, 2-chloropropyl, 3-chloropropyl,2,3-dichloropropyl, 2-bromopropyl, 3-bromopropyl, 3,3,3-trifluoropropyl,3,3,3-trichloropropyl, 2,2,3,3,3-pentafluoropropyl, heptafluoropropyl,1-(fluoromethyl)-2-fluoroethyl, 1-(chloromethyl)-2-chloroethyl,1-(bromomethyl)-2-bromoethyl, 4-fluorobutyl, 4-chlorobutyl, 4-bromobutyland nonafluorobutyl;

C₁-C₄-alkoxy: for example methoxy, ethoxy, propoxy, 1-methylethoxy,butoxy, 1-methylpropoxy, 2-methylpropoxy and 1,1-dimethylethoxy;

C₁-C₆-alkoxy: C₁-C₄-alkoxy as mentioned above, and also, for example,pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy,1,1-dimethylpropoxy, 1,2-dimethylpropoxy, 2,2-dimethylpropoxy,1-ethylpropoxy, hexoxy, 1-methylpentoxy, 2-methylpentoxy,3-methylpentoxy, 4-methylpentoxy, 1,1-dimethylbutoxy,1,2-dimethylbutoxy, 1,3-dimethylbutoxy, 2,2-dimethylbutoxy,2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1-ethylbutoxy, 2-ethylbutoxy,1,1,2-trimethylpropoxy, 1,2,2-trimethylpropoxy, 1-ethyl-1-methylpropoxyand 1-ethyl-2-methylpropoxy;

C₁-C₄-haloalkoxy: a C₁-C₄-alkoxy radical as mentioned above which ispartially or fully substituted by fluorine, chlorine, bromine and/oriodine, i.e., for example, fluoromethoxy, difluoromethoxy,trifluoromethoxy, chlorodifluoromethoxy, bromodifluoromethoxy,2-fluoroethoxy, 2-chloroethoxy, 2-bromomethoxy, 2-iodoethoxy,2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy,2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy,2,2,2-trichloroethoxy, pentafluoroethoxy, 2-fluoropropoxy,3-fluoropropoxy, 2-chloropropoxy, 3-chloropropoxy, 2-bromopropoxy,3-bromopropoxy, 2,2-difluoropropoxy, 2,3-difluoropropoxy,2,3-dichloropropoxy, 3,3,3-trifluoropropoxy, 3,3,3-trichloropropoxy,2,2,3,3,3-pentafluoropropoxy, heptafluoropropoxy,1-(fluoromethyl)-2-fluoroethoxy, 1-(chloromethyl)-2-chloroethoxy,1-(bromomethyl)-2-bromoethoxy, 4-fluorobutoxy, 4-chlorobutoxy,4-bromobutoxy and nonafluorobutoxy;

C₁-C₄-alkylthio, and the alkylthio moieties ofC₁-C₄-(alkylthio)carbonyloxy: for example methylthio, ethylthio,propylthio, 1-methylethylthio, butylthio, 1-methylpropylthio,2-methylpropylthio and 1,1-dimethylethylthio;

C₁-C₄-haloalkylthio: a C₁-C₄-alkylthio radical as mentioned above whichis partially or fully substituted by fluorine, chlorine, bromine and/oriodine, i.e., for example, fluoromethylthio, difluoromethylthio,trifluoromethylthio, chlorodifluoromethylthio, bromodifluoromethylthio,2-fluoroethylthio, 2-chloroethylthio, 2-bromoethylthio, 2-iodoethylthio,2,2-difluoroethylthio, 2,2,2-trifluoroethylthio,2,2,2-trichloroethylthio, 2-chloro-2-fluoroethylthio,2-chloro-2,2-difluoroethylthio, 2,2-dichloro-2-fluoroethylthio,pentafluoroethylthio, 2-fluoropropylthio, 3-fluoropropylthio,2-chloropropylthio, 3-chloropropylthio, 2-bromopropylthio,3-bromopropylthio, 2,2-difluoropropylthio, 2,3-difluoropropylthio,2,3-dichloropropylthio, 3,3,3-trifluoropropylthio,3,3,3-trichloropropylthio, 2,2,3,3,3-pentafluoropropylthio,heptafluoropropylthio, 1-(fluoromethyl)-2-fluoroethylthio,1-(chloromethyl)-2-chloroethylthio, 1-(bromomethyl)-2-bromoethylthio,4-fluorobutylthio, 4-chlorobutylthio, 4-bromobutylthio andnonafluorobutylthio;

C₁-C₄-alkylsulfonyl (C₁-C₄-alkyl-S(═0)₂-), and the alkylsulfonylmoieties of C₁-C₄-alkylsulfonyloxy: for example methylsulfonyl,ethylsulfonyl, propylsulfonyl, 1-methylethylsulfonyl, butylsulfonyl,1-methylpropylsulfonyl, 2-methylpropylsulfonyl and1,1-dimethylethylsulfonyl;

C₁-C₆-alkylsulfonyl, and the alkylsulfonyl moieties ofC₁-C6-alkylsulfonyloxy: a C₁-C₄-alkylsulfonyl radical as mentionedabove, and also, for example, pentylsulfonyl, 1-methylbutylsulfonyl,2-methylbutylsulfonyl, 3-methylbutylsulfonyl,1,1-dimethylpropylsulfonyl, 1,2-dimethylpropylsulfonyl,2,2-dimethylpropylsulfonyl, 1-ethylpropylsulfonyl, hexylsulfonyl,1-methylpentylsulfonyl, 2-methylpentylsulfonyl, 3-methylpentylsulfonyl,4-methylpentylsulfonyl, 1,1-dimethylbutylsulfonyl,1,2-dimethylbutylsulfonyl, 1,3-dimethylbutylsulfonyl,2,2-dimethylbutylsulfonyl, 2,3-dimethylbutylsulfonyl,3,3-dimethylbutylsulfonyl, 1-ethylbutylsulfonyl, 2-ethylbutylsulfonyl,1,1,2-trimethylpropylsulfonyl, 1,2,2-trimethylpropylsulfonyl,1-ethyl-1-methylpropylsulfonyl and 1-ethyl-2-methylpropylsulfonyl;

C₁-C₄-haloalkylsulfonyl: a C₁-C₄-alkylsulfonyl radical as mentionedabove which is partially or fully substituted by fluorine, chlorine,bromine and/or iodine, i.e., for example, fluoromethylsulfonyl,difluoromethylsulfonyl, trifluoromethylsulfonyl,chlorodifluoromethylsulfonyl, bromodifluoromethylsulfonyl,2-fluoroethylsulfonyl, 2-chloroethylsulfonyl, 2-bromoethylsulfonyl,2-iodoethylsulfonyl, 2,2-difluoroethylsulfonyl,2,2,2-trifluoroethylsulfonyl, 2-chloro-2-fluoroethylsulfonyl,2-chloro-2,2-difluoroethylsulfonyl, 2,2-dichloro-2-fluoroethylsulfonyl,2,2,2-trichloroethylsulfonyl, pentafluoroethylsulfonyl,2-fluoropropylsulfonyl, 3-fluoropropylsulfonyl, 2-chloropropylsulfonyl,3-chloropropylsulfonyl, 2-bromopropylsulfonyl, 3-bromopropylsulfonyl,2,2-difluoropropylsulfonyl, 2,3-difluoropropylsulfonyl,2,3-dichloropropylsulfonyl, 3,3,3-trifluoropropylsulfonyl,3,3,3-trichloropropylsulfonyl, 2,2,3,3,3-pentafluoropropylsulfonyl,heptafluoropropylsulfonyl, 1-(fluoromethyl)-2-fluoroethylsulfonyl,1-(chloromethyl)-2-chloroethylsulfonyl,1-(bromomethyl)-2-bromoethylsulfonyl, 4-fluorobutylsulfonyl,4-chlorobutylsulfonyl, 4-bromobutylsulfonyl and nonafluorobutylsulfonyl;

C₃-C₆-alkenyloxy: for example prop-1-en-1-yloxy, prop-2-en-1-yloxy,1-methylethenyloxy, buten-1-yloxy, buten-2-yloxy, buten-3-yloxy,1-methylprop-1-en-1-yloxy, 2-methylprop-1-en-1-yloxy,1-methylprop-2-en-1-yloxy, 2-methylprop-2-en-1-yloxy, penten-1-yloxy,penten-2-yloxy, penten-3-yloxy, penten-4-yloxy,1-methylbut-1-en-1-yloxy, 2-methylbut-1-en-1-yloxy,3-methylbut-1-en-1-yloxy, 1-methylbut-2-en-1-yloxy,2-methylbut-2-en-1-yloxy, 3-methylbut-2-en-1-yloxy,1-methylbut-3-en-1-yloxy, 2-methylbut-3-en-1-yloxy,3-methylbut-3-en-1-yloxy, 1,1-dimethylprop-2-en-1-yloxy,1,2-dimethylprop-1-en-1-yloxy, 1,2-dimethylprop-2-en-1-yloxy,1-ethylprop-1-en-2-yloxy, 1-ethylprop-2-en-1-yloxy, hex-1-en-1-yloxy,hex-2-en-1-yloxy, hex-3-en-1-yloxy, hex-4-en-1-yloxy, Hex-5-en-1-yloxy,1-methylpent-1-en-1-yloxy, 2-methylpent-1-en-1-yloxy,3-methylpent-1-en-1-yloxy, 4-methylpent-1-en-1-yloxy,1-methylpent-2-en-1-yloxy, 2-methylpent-2-en-1-yloxy,3-methylpent-2-en-1-yloxy, 4-methylpent-2-en-1-yloxy,1-methylpent-3-en-1-yloxy, 2-methylpent-3-en-1-yloxy,3-methylpent-3-en-1-yloxy, 4-methylpent-3-en-1-yloxy,1-methylpent-4-en-1-yloxy, 2-methylpent-4-en-1-yloxy,3-methylpent-4-en-1-yloxy, 4-methylpent-4-en-1-yloxy,1,1-dimethylbut-2-en-1-yloxy, 1,1-dimethylbut-3-en-1-yloxy,1,2-dimethylbut-3-en-1-yloxy, 1,2-dimethylbut-2-en-1-yloxy,1,2-dimethylbut-3-en-1-yloxy, 1,3-dimethylbut-3-en-1-yloxy,1,3-dimethylbut-2-en-1-yloxy, 1,3-dimethylbut-3-en-1-yloxy,2,2-dimethylbut-3-en-1-yloxy, 2,3-dimethylbut-3-en-1-yloxy,2,3-dimethylbut-2-en-1-yloxy, 2,3-dimethylbut-3-en-1-yloxy,3,3-dimethylbut-1-en-1-yloxy, 3,3-dimethylbut-2-en-1-yloxy,1-ethylbut-3-en-1-yloxy, 1-ethylbut-2-en-1-yloxy,1-ethylbut-3-en-1-yloxy, 2-ethylbut-3-en-1-yloxy,2-ethylbut-2-en-1-yloxy, 2-ethylbut-3-en-1-yloxy,1,1,2-trimethylprop-2-en-1-yloxy, 1-ethyl-1-methylprop-2-en-1-yloxy,1-ethyl-2-methylprop-1-en-1-yloxy and 1-ethyl-2-methylprop-2-en-1-yloxy;

C₃-C₆-alkenyl: prop-1-en-1-yl, prop-2-en-1-yl, 1-methylethenyl,buten-1-yl, buten-2-yl, buten-3-yl, 1-methylprop-1-en-1-yl,2-methylprop-1-en-1-yl, 1-methylprop-2-en-1-yl, 2-methylprop-2-en-1-yl,penten-1-yl, penten-2-yl, penten-3-yl, penten-4-yl,1-methylbut-1-en-1-yl, 2-methylbut-1-en-1-yl, 3-methylbut-1-en-1-yl,1-methylbut-2-en-1-yl, 2-methylbut-2-en-1-yl, 3-methylbut-2-en-1-yl,1-methylbut-3-en-1-yl, 2-methylbut-3-en-1-yl, 3-methylbut-3-en-1-yl,1,1-dimethylprop-2-en-1-yl, 1,2-dimethylprop-1-en-1-yl,1,2-dimethylprop-2-en-1-yl, 1-ethylprop-1-en-2-yl,1-ethylprop-2-en-1-yl, hex-1-en-1-yl, hex-2-en-1-yl, hex-3-en-1-yl,hex-4-en-1-yl, hex-5-en-1-yl, 1-methylpent-1-en-1-yl,2-methylpent-1-en-1-yl, 3-methylpent-1-en-1-yl, 4-methylpent-1-en-1-yl,1-methylpent-2-en-1-yl, 2-methylpent-2-en-1-yl, 3-methylpent-2-en-1-yl,4-methylpent-2-en-1-yl, 1-methylpent-3-en-1-yl, 2-methylpent-3-en-1-yl,3-methylpent-3-en-1-yl, 4-methylpent-3-en-1-yl, 1-methylpent-4-en-1-yl,2-methylpent-4-en-1-yl, 3-methylpent-4-en-1-yl, 4-methylpent-4-en-1-yl,1,1-dimethylbut-2-en-1-yl, 1,1-dimethylbut-3-en-1-yl,1,2-dimethylbut-1-en-1-yl, 1,2-dimethylbut-2-en-1-yl,1,2-dimethylbut-3-en-1-yl, 1,3-dimethylbut-1-en-1-yl,1,3-dimethylbut-2-en-1-yl, 1,3-dimethylbut-3-en-1-yl,2,2-dimethylbut-3-en-1-yl, 2,3-dimethylbut-1-en-1-yl,2,3-dimethylbut-2-en-1-yl, 2,3-dimethylbut-3-en-1-yl,3,3-dimethylbut-1-en-1-yl, 3,3-dimethylbut-2-en-1-yl,1-ethylbut-1-en-1-yl, 1-ethylbut-2-en-1-yl, 1-ethylbut-3-en-1-yl,2-ethylbut-1-en-1-yl, 2-ethylbut-2-en-1-yl, 2-ethylbut-3-en-1-yl,1,1,2-trimethylprop-2-en-1-yl, 1-ethyl1-1-methylprop-2-en-1-yl,1-ethyl-2-methylprop-1-en-1-yl and 1-ethyl-2-methylprop-2-en-1-yl.

The phenyl rings are preferably unsubstituted or carry one to threehalogen atoms and/or one nitro group, one cyano group, one or twomethyl, trifluoromethyl, methoxy or trifluoromethoxy groups.

Emphasis is given to those 3-(heterocyclyl)-substituted benzoylpyrazolesof the formula I where

R⁷ is hydroxyl, C₁-C₆-alkoxy, C₃-C₆-alkenyloxy, C₁-C₆-alkyl-sulfonyloxy,C₁-C₆-alkylcarbonyloxy, phenylsulfonyloxy or phenylcarbonyloxy, wherethe phenyl radical of the two last-mentioned substituents may bepartially or fully halogenated and/or may carry one to three of thefollowing groups: nitro, cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl,C₁-C₄-alkoxy or C₁-C₄-haloalkoxy.

Preference is given to the 3-(heterocyclyl)-substituted benzoylpyrazolesof the formula I where:

X is O;

R¹ is C₁-C₄-alkyl;

particularly preferably methyl or ethyl;

with particular preference methyl;

R², R³, R⁴, R⁵ are hydrogen, C₁-C₄-alkyl or C₁-C₄-haloalkyl;

particularly preferably hydrogen, methyl, ethyl, propyl, 1-methylethyl,fluoromethyl or chloromethyl;

with particular preference hydrogen, methyl, ethyl or chloromethyl;

R⁶ is C₁-C₄-alkylthio or C₁-C₄-alkylsulfonyl;

particularly preferably methylthio, ethylthio or 1-methyl-1-ethylthio,methylsulfonyl, ethylsulfonyl, 1-methylethylsulfonyl or

propylsulfonyl;

with particular preference methylsulfonyl, ethylsulfonyl,1-methylethylsulfonyl or propylsulfonyl;

R⁷ is hydroxyl, C₁-C₆-alkoxy, C₃-C₆-alkenyloxy, C₁-C₆-alkylsulfonyloxy,C₁-C6-alkylcarbonyloxy, C₁-C₄-(alkylthio)carbonyloxy, phenylsulfonyloxyor phenylcarbonyloxy, where the phenyl radical of the two last-mentionedsubstituents may be partially or fully halogenated and/or may carry oneto three of the following groups:

nitro, cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy orC₁-C₄-haloalkoxy;

particularly preferably hydroxyl, C₁-C₄-alkoxy, C₃-C₆-alkenyloxy,C₁-C₄-alkylsulfonyloxy, C₁-C₄-alkylcarbonyloxy, phenylsulfonyloxy orphenylcarbonyloxy, where the phenyl radical of the two last-mentionedsubstituents may be partially or fully halogenated and/or may carry oneto three of the following groups:

nitro, cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy orC₁-C₄-haloalkoxy;

R⁸, R⁹ are C₁-C₄-alkyl;

particularly preferably methyl, ethyl, propyl, 1-methyl-1-ethyl, butyl,1-methyl-1-propyl and 2-methyl-1-propyl;

R¹⁰ is hydrogen or C₁-C4-alkyl;

particularly preferably C₁-C₄-alkyl;

with particular preference methyl, ethyl or propyl;

R¹¹ is hydrogen or C₁-C₄-alkyl;

particularly preferably hydrogen or methyl.

Particular preference is given to the 3-(heterocyclyl)-substitutedbenzoylpyrazoles of the formula I where

X is O;

R¹ is C₁-C₄-alkyl;

particularly preferably methyl or ethyl;

with particular preference methyl;

R⁶ is C₁ -C₄-alkylsulfonyl; particularly preferably methylsulfonyl,ethylsulfonyl, 1-methyl-1-ethylsulfonyl or propylsulfonyl;

R⁷ is hydroxyl, C₁-C₆-alkylsulfonyloxy, C₁-C₆-alkylcarbonyloxy,phenylsulfonyloxy or phenylcarbonyloxy, where the phenyl radical of thetwo last-mentioned substituents may be partially or fully halogenatedand/or may carry one to three of the following groups:

nitro, cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy orC₁-C₄-haloalkoxy; particularly preferably hydroxyl;

R⁸, R⁹ are C₁-C₄-alkyl;

R¹⁰ is hydrogen or C₁-C4-alkyl.

Very particular preference is given to the 3-(heterocyclyl)-substitutedbenzoylpyrazoles of the formula I where

R⁸ is C₂-C₄-alkyl, for example ethyl, 1-methyl-1-ethyl, propyl or butyl;

R⁹ is C₁-C₄-alkyl, for example methyl or ethyl;

R¹⁰ is hydrogen or C₁-C₄-alkyl, for example methyl or ethyl.

Very particular preference is also given to the3-(heterocyclyl)-substituted benzoylpyrazoles of the formula I where

R⁸ is methyl;

R⁹ is C₁-C₄-alkyl, for example methyl, ethyl, propyl or butyl;

R¹⁰ is C₁-C₄-alkyl, for example methyl or ethyl.

Very particular preference is also given to the3-(heterocyclyl)-substituted benzoylpyrazoles of the formula I where

R⁸, R⁹ are methyl;

R¹⁰ is hydrogen.

Preference is also given to the 3-(heterocyclyl)-substitutedbenzoylpyrazoles of the formula I where:

X is O

R¹ is C₁-C₄-alkyl; particularly preferably methyl or ethyl; withparticular preference methyl;

R², R³, R⁴, R⁵ are hydrogen, C₁-C₄-alkyl or C₁-C₄-haloalkyl;particularly preferably hydrogen, methyl, ethyl, propyl,1-methyl-1-ethyl, chloromethyl or fluoromethyl;

with particular preference hydrogen, methyl, ethyl or chloromethyl;

R⁶ is halogen, nitro, C₁-C₄-haloalkyl, C₁-C₄-alkoxy or C₁-C₄-haloalkoxy;

particularly preferably halogen, such as chlorine or bromine, nitro,C₁-C₂-haloalkyl, such as difluoromethyl or trifluoromethyl, C₁-C₂-alkoxyor C₁-C₂-haloalkoxy, such as difluoromethoxy, chlorodifluoromethoxy ortrifluoromethoxy;

R⁷ is hydroxyl, C₁-C₆-alkoxy, C₃-C₆-alkenyloxy, C₁-C₆-alkylsulfonyloxy,C₁-C₆-alkylcarbonyloxy, C₁-C₄-(alkylthio)carbonyloxy, phenylsulfonyloxyor phenylcarbonyloxy, where the phenyl radical of the two last-mentionedsubstituents may be partially or fully halogenated and/or may carry oneto three of the following groups:

nitro, cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy orC₁-C₄-haloalkoxy;

particularly preferably hydroxyl, C₁-C₄-alkoxy, C₃-C₆-alkenyloxy,C₁-C₄-alkylsulfonyloxy, C₁-C₄-alkylcarbonyloxy, phenylsulfonyloxy orphenylcarbonyloxy, where the phenyl radical of the two last-mentionedsubstituents may be partially or fully halogenated and/or may carry oneto three of the following groups:

nitro, cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy orC₁-C₄-haloalkoxy;

R⁸, R⁹ are C₁-C₄-alkyl; particularly preferably methyl, ethyl, propyl,1-methyl-1-ethyl, butyl, 1-methyl-1-propyl and 2-methyl-1-propyl;

R¹⁰ is hydrogen or C₁-C₄-alkyl; particularly preferably C₁-C₄-alkyl;with particular preference methyl, ethyl or propyl;

R¹¹ is hydrogen or C₁-C₄-alkyl; particularly preferably hydrogen ormethyl.

Particular preference is given to the 3-(heterocyclyl)-substitutedbenzoylpyrazoles of the formula I where

X is O

R¹ is C₁-C₄-alkyl; particularly preferably methyl or ethyl; withparticular preference methyl;

R⁶ is halogen, nitro, C₁-C₄-haloalkyl, C₁-C₄-alkoxy or C₁-C₄-haloalkoxy;

particularly preferably halogen, such as chlorine a or bromine, nitro,C₁-C₂-haloalkyl, such as difluoromethyl or trifluoromethyl, C₁-C₂-alkoxyor C₁-C₂-haloalkoxy, such as difluoromethoxy;

R⁷ is hydroxyl, C₁-C₆-alkylsulfonyloxy, C₁-C₆-alkylcarbonyloxy,phenylsulfonyloxy or phenylcarbonyloxy, where the phenyl radical of thetwo last-mentioned substituents may be partially or fully halogenatedand/or may carry one to three of the following groups:

nitro, cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy orC₁-C₄-haloalkoxy; particularly preferably hydroxyl;

R⁸, R⁹ are C₁-C₄-alkyl;

R¹⁰ is hydrogen or C₁-C₄-alkyl.

very particular preference is given to the 3-(heterocyclyl)-substitutedbenzoylpyrazoles of the formula I where

R⁸ is C₂-C₄-alkyl, for example ethyl, 1-methyl-1-ethyl, propyl or butyl;

R⁹ is C₁-C₄-alkyl, for example methyl or ethyl;

R¹⁰ is hydrogen or C₁-C₄-alkyl, for example methyl or ethyl.

Very particular preference is also given to the3-(heterocyclyl)-substituted benzoylpyrazoles of the formula I where

R⁸ is methyl;

R⁹ is C₁-C₄-alkyl, for example methyl, ethyl, propyl or butyl;

R¹⁰ is C₁-C₄-alkyl, for example methyl or ethyl.

Very particular preference is also given to the3-(heterocyclyl)-substituted benzoylpyrazoles of the formula I where

R⁸, R⁹ are methyl;

R¹⁰ is hydrogen.

Preference is also given to the 3-(heterocyclyl)-substitutedbenzoylpyrazoles of the formula I where:

X is N(C₁-C₆-alkyl);

particularly preferably N-methyl, N-ethyl, N-(1-methyl-1-ethyl) orN-propyl;

R¹ is C₁-C6-alkyl;

particularly preferably methyl or ethyl;

with particular preference methyl;

R², R³, R⁴, R⁵ are hydrogen, C₁-C₄-alkyl or C₁-C₄-haloalkyl;

particularly preferably hydrogen, methyl, ethyl, propyl,1-methyl-1-ethyl, fluoromethyl or chloromethyl; with particularpreference hydrogen, methyl, ethyl or chloromethyl;

R⁶ is halogen, nitro, C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy,C₁-C₄-alkylthio, C₁-C₄-haloalkylthio, C₁-C₄-alkylsulfonyl orC₁-C₄-haloalkylsulfonyl;

particularly preferably halogen, such as fluorine, chlorine or bromine,nitro, C₁-C₄-haloalkyl, such as difluoromethyl or trifluoromethyl,C₁-C₄-alkoxy, such as methoxy or ethoxy, C₁-C₄-haloalkoxy, such asdifluoromethoxy, chlorodifluoromethoxy or trifluoromethoxy,C₁-C₄-alkylthio, such as methylthio or ethylthio, orC₁-C₄-alkylsulfonyl, such as methylsulfonyl, ethylsulfonyl,1-methyl-1-ethylsulfonyl or propylsulfonyl;

R⁷ is hydroxyl, C₁-C₆-alkoxy, C₃-C₆-alkenyloxy, C₁-C₆-alkylsulfonyloxy,C₁-C₆-alkylcarbonyloxy, C₁-C₄-(alkylthio)carbonyloxy, phenylsulfonyloxyor phenylcarbonyloxy, where the phenyl radical of the two last-mentionedsubstituents may be partially or fully halogenated and/or may carry oneto three of the following groups:

nitro, cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy orC₁-C₄-haloalkoxy; particularly preferably hydroxyl, C₁-C₄-alkoxy,C₃-C₆-alkenyloxy, C₁-C₄-alkylsulfonyloxy, C₁-C₄-alkylcarbonyloxy,phenylsulfonyloxy or phenylcarbonyloxy, where the phenyl radical of thetwo last-mentioned substituents may be partially or fully halogenatedand/or may carry one to three of the following groups:

nitro, cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy orC₁-C₄-haloalkoxy;

R⁸, R⁹ are C₁-C₄-alkyl;

particularly preferably methyl, ethyl, propyl, 1-methyl-1-ethyl, butyl,1-methyl-1-propyl and 2-methyl-1-propyl;

R¹⁰ is hydrogen or C₁-C₄-alkyl;

particularly preferably C₁-C₄-alkyl;

with particular preference methyl, ethyl or propyl;

R¹¹ is hydrogen or C₁-C₄-alkyl; particularly preferably hydrogen ormethyl.

Particular preference is given to the 3-heterocyclyl-substitutedbenzoylpyrazoles of the formula I where

R⁷ is hydroxyl, C₁-C₆-alkylsulfonyloxy, C₁-C₆-alkylcarbonyloxy,phenylsulfonyloxy or phenylcarbonyloxy, where the phenyl radical of thetwo last-mentioned substituents may be partially or fully halogenatedand/or may carry one to three of the following groups:

nitro, cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy orC₁-C4-haloalkoxy;

particularly preferably hydroxyl.

Preference is likewise given to the 3-(heterocyclyl)-substitutedbenzoylpyrazoles of the formula I in which the variables are as definedbelow:

X is O;

R¹ is C₁-C₄-alkyl;

particularly preferably methyl or ethyl;

R², R³, R⁴, R⁵ are hydrogen, C₁-C₄-alkyl or C₁-C₄-haloalkyl;

particularly preferably hydrogen or C₁-C₄-haloalkyl;

R⁶ is C₁-C₄-alkylsulfonyl;

particularly preferably methylsulfonyl;

R⁷ is hydroxyl, C₁-C₆-alkoxy, C₁-C₆-alkylcarbonyloxy,C₁-C4-(alkylthio)carbonyloxy, phenylsulfonyloxy or phenylcarbonyloxy,where the phenyl radical of the two last-mentioned substituents may bepartially or fully halogenated and/or may carry one to three of thefollowing groups:

nitro, cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy orC₁-C₄-haloalkoxy;

particularly preferably hydroxyl, C₁-C₄-alkoxy or phenylcarbonyloxy,where the phenyl radical may be [lacuna] or fully halogenated and/or maycarry one to three C₁-C₄-haloalkyl radicals;

R⁸, R⁹ are C₁-C₄-alkyl;

R¹⁰ is hydrogen or C₁-C₄-alkyl;

R¹¹ is hydrogen or C₁-C₄-alkyl.

Very particular preference is given to the compounds of the formula Ia1(≡I where R¹, R⁸, R⁹ =CH₃; R¹⁰, R¹¹=H), in particular to the compoundsIa1.1 to Ia1.300 of Table 1, where the radical definitions X and R¹ toR¹¹ are of particular importance for the compounds according to theinvention, not only in combination with one another, but in each casealso on their own.

TABLE 1 No. X R² R³ R⁴ R⁵ R⁶ R⁷ Ia1.1 O H H H H SCH₃ OH Ia1.2 O H H H HSCH₂CH₃ OH Ia1.3 O H H H H SO₂CH₃ OH Ia1.4 O H H H H SO₂CH₂CH₃ OH Ia1.5O H H H H SO₂CH(CH₃)₂ OH Ia1.6 O H H H H SO₂(CH₂)₂CH₃ OH Ia1.7 O H H H HCl OH Ia1.8 O H H H H Br OH Ia1.9 O H H H H NO₂ OH Ia1.10 O H H H H CHF₂OH Ia1.11 O H H H H CF₃ OH Ia1.12 O H H H H OCH₃ OH Ia1.13 O H H H HOCH₂CH₃ OH Ia1.14 O H H H H OCHF₂ OH Ia1.15 O H H H H OCF₃ OH Ia1.16 OCH₃ H H H SCH₃ OH Ia1.17 O CH₃ H H H SCH₂CH₃ OH Ia1.18 O CH₃ H H HSO₂CH₃ OH Ia1.19 O CH₃ H H H SO₂CH₂CH₃ OH Ia1.20 O CH₃ H H H SO₂CH(CH₃)₂OH Ia1.21 O CH₃ H H H SO₂(CH₂)₂CH₃ OH Ia1.22 O CH₃ H H H Cl OH Ia1.23 OCH₃ H H H Br OH Ia1.24 O CH₃ H H H NO₂ OH Ia1.25 O CH₃ H H H CHF₂ OHIa1.26 O CH₃ H H H CF₃ OH Ia1.27 O CH₃ H H H OCH₃ OH Ia1.28 O CH₃ H H HOCH₂CH₃ OH Ia1.29 O CH₃ H H H OCHF₂ OH Ia1.30 O CH₃ H H H OCF₃ OH Ia1.31O H H CH₃ H SCH₃ OH Ia1.32 O H H CH₃ H SCH₂CH₃ OH Ia1.33 O H H CH₃ HSO₂CH₃ OH Ia1.34 O H H CH₃ H SO₂CH₂CH₃ OH Ia1.35 O H H CH₃ H SO₂CH(CH₃)₂OH Ia1.36 O H H CH₃ H SO₂(CH₂)₂CH₃ OH Ia1.37 O H H CH₃ H Cl OH Ia1.38 OH H CH₃ H Br OH Ia1.39 O H H CH₃ H NO₂ OH Ia1.40 O H H CH₃ H CHF₂ OHIa1.41 O H H CH₃ H CF₃ OH Ia1.42 O H H CH₃ H OCH₃ OH Ia1.43 O H H CH₃ HOCH₂CH₃ OH Ia1.44 O H H CH₃ H OCHF₂ OH Ia1.45 O H H CH₃ H OCF₃ OH Ia1.46O CH₃ CH₃ H H SCH₃ OH Ia1.47 O CH₃ CH₃ H H SCH₂CH₃ OH Ia1.48 O CH₃ CH₃ HH SO₂CH₃ OH Ia1.49 O CH₃ CH₃ H H SO₂CH₂CH₃ OH Ia1.50 O CH₃ CH₃ H HSO₂CH(CH₃)₂ OH Ia1.51 O CH₃ CH₃ H H SO₂(CH₂)₂CH₃ OH Ia1.52 O CH₃ CH₃ H HCl OH Ia1.53 O CH₃ CH₃ H H Br OH Ia1.54 O CH₃ CH₃ H H NO₂ OH Ia1.55 OCH₃ CH₃ H H CHF₂ OH Ia1.56 O CH₃ CH₃ H H CF₃ OH Ia1.57 O CH₃ CH₃ H HOCH₃ OH Ia1.58 O CH₃ CH₃ H H OCH₂CH₃ OH Ia1.59 O CH₃ CH₃ H H OCHF₂ OHIa1.60 O CH₃ CH₃ H H OCF₃ OH Ia1.61 O CH₃ H CH₃ H SCH₃ OH Ia1.62 O CH₃ HCH₃ H SCH₂CH₃ OH Ia1.63 O CH₃ H CH₃ H SO₂CH₃ OH Ia1.64 O CH₃ H CH₃ HSO₂CH₂CH₃ OH Ia1.65 O CH₃ H CH₃ H SO₂CH(CH₃)₂ OH Ia1.66 O CH₃ H CH₃ HSO₂(CH₂)₂CH₃ OH Ia1.67 O CH₃ H CH₃ H Cl OH Ia1.68 O CH₃ H CH₃ H Br OHIa1.69 O CH₃ H CH₃ H NO₂ OH Ia1.70 O CH₃ H CH₃ H CHF₂ OH Ia1.71 O CH₃ HCH₃ H CF₃ OH Ia1.72 O CH₃ H CH₃ H OCH₃ OH Ia1.73 O CH₃ H CH₃ H OCH₂CH₃OH Ia1.74 O CH₃ H CH₃ H OCHF₂ OH Ia1.75 O CH₃ H CH₃ H OCF₃ OH Ia1.76 O HH CH₃ CH₃ SCH₃ OH Ia1.77 O H H CH₃ CH₃ SCH₂CH₃ OH Ia1.78 O H H CH₃ CH₃SO₂CH₃ OH Ia1.79 O H H CH₃ CH₃ SO₂CH₂CH₃ OH Ia1.80 O H H CH₃ CH₃SO₂CH(CH₃)₂ OH Ia1.81 O H H CH₃ CH₃ SO₂(CH₂)₂CH₃ OH Ia1.82 O H H CH₃ CH₃Cl OH Ia1.83 O H H CH₃ CH₃ Br OH Ia1.84 O H H CH₃ CH₃ NO₂ OH Ia1.85 O HH CH₃ CH₃ CHF₂ OH Ia1.86 O H H CH₃ CH₃ CF₃ OH Ia1.87 O H H CH₃ CH₃ OCH₃OH Ia1.88 O H H CH₃ CH₃ OCH₂CH₃ OH Ia1.89 O H H CH₃ CH₃ OCHF₂ OH Ia1.90O H H CH₃ CH₃ OCF₃ OH Ia1.91 O CH₃ CH₃ CH₃ H SCH₃ OH Ia1.92 O CH₃ CH₃CH₃ H SCH₂CH₃ OH Ia1.93 O CH₃ CH₃ CH₃ H SO₂CH₃ OH Ia1.94 O CH₃ CH₃ CH₃ HSO₂CH₂CH₃ OH Ia1.95 O CH₃ CH₃ CH₃ H SO₂CH(CH₃)₂ OH Ia1.96 O CH₃ CH₃ CH₃H SO₂(CH₂)₂CH₃ OH Ia1.97 O CH₃ CH₃ CH₃ H Cl OH Ia1.98 O CH₃ CH₃ CH₃ H BrOH Ia1.99 O CH₃ CH₃ CH₃ H NO₂ OH Ia1.100 O CH₃ CH₃ CH₃ H CHF₂ OH Ia1.101O CH₃ CH₃ CH₃ H CF₃ OH Ia1.102 O CH₃ CH₃ CH₃ H OCH₃ OH Ia1.103 O CH₃ CH₃CH₃ H OCH₂CH₃ OH Ia1.104 O CH₃ CH₃ CH₃ H OCHF₂ OH Ia1.105 O CH₃ CH₃ CH₃H OCF₃ OH Ia1.106 O CH₃ H CH₃ CH₃ SCH₃ OH Ia1.107 O CH₃ H CH₃ CH₃SCH₂CH₃ OH Ia1.108 O CH₃ H CH₃ CH₃ SO₂CH₃ OH Ia1.109 O CH₃ H CH₃ CH₃SO₂CH₂CH₃ OH Ia1.110 O CH₃ H CH₃ CH₃ SO₂CH(CH₃)₂ OH Ia1.111 O CH₃ H CH₃CH₃ SO₂(CH₂)₂CH₃ OH Ia1.112 O CH₃ H CH₃ CH₃ Cl OH Ia1.113 O CH₃ H CH₃CH₃ Br OH Ia1.114 O CH₃ H CH₃ CH₃ NO₂ OH Ia1.115 O CH₃ H CH₃ CH₃ CHF₂ OHIa1.116 O CH₃ H CH₃ CH₃ CF₃ OH Ia1.117 O CH₃ H CH₃ CH₃ OCH₃ OH Ia1.118 OCH₃ H CH₃ CH₃ OCH₂CH₃ OH Ia1.119 O CH₃ H CH₃ CH₃ OCHF₂ OH Ia1.120 O CH₃H CH₃ CH₃ OCF₃ OH Ia1.121 O CH₃ CH₃ CH₃ CH₃ SCH₃ OH Ia1.122 O CH₃ CH₃CH₃ CH₃ SCH₂CH₃ OH Ia1.123 O CH₃ CH₃ CH₃ CH₃ SO₂CH₃ OH Ia1.124 O CH₃ CH₃CH₃ CH₃ SO₂CH₂CH₃ OH Ia1.125 O CH₃ CH₃ CH₃ CH₃ SO₂CH(CH₃)₂ OH Ia1.126 OCH₃ CH₃ CH₃ CH₃ SO₂(CH₂)₂CH₃ OH Ia1.127 O CH₃ CH₃ CH₃ CH₃ Cl OH Ia1.128O CH₃ CH₃ CH₃ CH₃ Br OH Ia1.129 O CH₃ CH₃ CH₃ CH₃ NO₂ OH Ia1.130 O CH₃CH₃ CH₃ CH₃ CHF₂ OH Ia1.131 O CH₃ CH₃ CH₃ CH₃ CF₃ OH Ia1.132 O CH₃ CH₃CH₃ CH₃ OCH₃ OH Ia1.133 O CH₃ CH₃ CH₃ CH₃ OCH₂CH₃ OH Ia1.134 O CH₃ CH₃CH₃ CH₃ OCHF₂ OH Ia1.135 O CH₃ CH₃ CH₃ CH₃ OCF₃ OH Ia1.136 O CH₂Cl H H HSCH₃ OH Ia1.137 O CH₂Cl H H H SCH₂CH₃ OH Ia1.138 O CH₂Cl H H H SO₂CH₃ OHIa1.139 O CH₂Cl H H H SO₂CH₂CH₃ OH Ia1.140 O CH₂Cl H H H SO₂CH(CH₃)₂ OHIa1.141 O CH₂Cl H H H SO₂(CH₂)₂CH₃ OH Ia1.142 O CH₂Cl H H H Cl OHIa1.143 O CH₂Cl H H H Br OH Ia1.144 O CH₂Cl H H H NO₂ OH Ia1.145 O CH₂ClH H H CHF₂ OH Ia1.146 O CH₂Cl H H H CF₃ OH Ia1.147 O CH₂Cl H H H OCH₃ OHIa1.148 O CH₂Cl H H H OCH₂CH₃ OH Ia1.149 O CH₂Cl H H H OCHF₂ OH Ia1.150O CH₂Cl H H H OCF₃ OH Ia1.151 NCH₃ H H H H SCH₃ OH Ia1.152 NCH₃ H H H HSCH₂CH₃ OH Ia1.153 NCH₃ H H H H SO₂CH₃ OH Ia1.154 NCH₃ H H H H SO₂CH₂CH₃OH Ia1.155 NCH₃ H H H H SO₂CH(CH₃)₂ OH Ia1.156 NCH₃ H H H H SO₂(CH₂)₂CH₃OH Ia1.157 NCH₃ H H H H Cl OH Ia1.158 NCH₃ H H H H Br OH Ia1.159 NCH₃ HH H H NO₂ OH Ia1.160 NCH₃ H H H H CHF₂ OH Ia1.161 NCH₃ H H H H CF₃ OHIa1.162 NCH₃ H H H H OCH₃ OH Ia1.163 NCH₃ H H H H OCH₂CH₃ OH Ia1.164NCH₃ H H H H OCHF₂ OH Ia1.165 NCH₃ H H H H OCF₃ OH Ia1.166 NCH₃ CH₃ H HH SCH₃ OH Ia1.167 NCH₃ CH₃ H H H SCH₂CH₃ OH Ia1.168 NCH₃ CH₃ H H HSO₂CH₃ OH Ia1.169 NCH₃ CH₃ H H H SO₂CH₂CH₃ OH Ia1.170 NCH₃ CH₃ H H HSO₂CH(CH₃)₂ OH Ia1.171 NCH₃ CH₃ H H H SO₂(CH₂)₂CH₃ OH Ia1.172 NCH₃ CH₃ HH H Cl OH Ia1.173 NCH₃ CH₃ H H H Br OH Ia1.174 NCH₃ CH₃ H H H NO₂ OHIa1.175 NCH₃ CH₃ H H H CHF₂ OH Ia1.176 NCH₃ CH₃ H H H CF₃ OH Ia1.177NCH₃ CH₃ H H H OCH₃ OH Ia1.178 NCH₃ CH₃ H H H OCH₂CH₃ OH Ia1.179 NCH₃CH₃ H H H OCHF₂ OH Ia1.180 NCH₃ CH₃ H H H OCF₃ OH Ia1.181 NCH₃ H H CH₃ HSCH₃ OH Ia1.182 NCH₃ H H CH₃ H SCH₂CH₃ OH Ia1.183 NCH₃ H H CH₃ H SO₂CH₃OH Ia1.184 NCH₃ H H CH₃ H SO₂CH₂CH₃ OH Ia1.185 NCH₃ H H CH₃ HSO₂CH(CH₃)₂ OH Ia1.186 NCH₃ H H CH₃ H SO₂(CH₂)₂CH₃ OH Ia1.187 NCH₃ H HCH₃ H Cl OH Ia1.188 NCH₃ H H CH₃ H Br OH Ia1.189 NCH₃ H H CH₃ H NO₂ OHIa1.190 NCH₃ H H CH₃ H CHF₂ OH Ia1.191 NCH₃ H H CH₃ H CF₃ OH Ia1.192NCH₃ H H CH₃ H OCH₃ OH Ia1.193 NCH₃ H H CH₃ H OCH₂CH₃ OH Ia1.194 NCH₃ HH CH₃ H OCHF₂ OH Ia1.195 NCH₃ H H CH₃ H OCF₃ OH Ia1.196 NCH₃ CH₃ CH₃ H HSCH₃ OH Ia1.197 NCH₃ CH₃ CH₃ H H SCH₂CH₃ OH Ia1.198 NCH₃ CH₃ CH₃ H HSO₂CH₃ OH Ia1.199 NCH₃ CH₃ CH₃ H H SO₂CH₂CH₃ OH Ia1.200 NCH₃ CH₃ CH₃ H HSO₂CH(CH₃)₂ OH Ia1.201 NCH₃ CH₃ CH₃ H H SO₂(CH₂)₂CH₃ OH Ia1.202 NCH₃ CH₃CH₃ H H Cl OH Ia1.203 NCH₃ CH₃ CH₃ H H Br OH Ia1.204 NCH₃ CH₃ CH₃ H HNO₂ OH Ia1.205 NCH₃ CH₃ CH₃ H H CHF₂ OH Ia1.206 NCH₃ CH₃ CH₃ H H CF₃ OHIa1.207 NCH₃ CH₃ CH₃ H H OCH₃ OH Ia1.208 NCH₃ CH₃ CH₃ H H OCH₂CH₃ OHIa1.209 NCH₃ CH₃ CH₃ H H OCHF₂ OH Ia1.210 NCH₃ CH₃ CH₃ H H OCF₃ OHIa1.211 NCH₃ CH₃ H CH₃ H SCH₃ OH Ia1.212 NCH₃ CH₃ H CH₃ H SCH₂CH₃ OHIa1.213 NCH₃ CH₃ H CH₃ H SO₂CH₃ OH Ia1.214 NCH₃ CH₃ H CH₃ H SO₂CH₂CH₃ OHIa1.215 NCH₃ CH₃ H CH₃ H SO₂CH(CH₃)₂ OH Ia1.216 NCH₃ CH₃ H CH₃ HSO₂(CH₂)₂CH₃ OH Ia1.217 NCH₃ CH₃ H CH₃ H Cl OH Ia1.218 NCH₃ CH₃ H CH₃ HBr OH Ia1.219 NCH₃ CH₃ H CH₃ H NO₂ OH Ia1.220 NCH₃ CH₃ H CH₃ H CHF₂ OHIa1.221 NCH₃ CH₃ H CH₃ H CF₃ OH Ia1.222 NCH₃ CH₃ H CH₃ H OCH₃ OH Ia1.223NCH₃ CH₃ H CH₃ H OCH₂CH₃ OH Ia1.224 NCH₃ CH₃ H CH₃ H OCHF₂ OH Ia1.225NCH₃ CH₃ H CH₃ H OCF₃ OH Ia1.226 NCH₃ H H CH₃ CH₃ SCH₃ OH Ia1.227 NCH₃ HH CH₃ CH₃ SCH₂CH₃ OH Ia1.228 NCH₃ H H CH₃ CH₃ SO₂CH₃ OH Ia1.229 NCH₃ H HCH₃ CH₃ SO₂CH₂CH₃ OH Ia1.230 NCH₃ H H CH₃ CH₃ SO₂CH(CH₃)₂ OH Ia1.231NCH₃ H H CH₃ CH₃ SO₂(CH₂)₂CH₃ OH Ia1.232 NCH₃ H H CH₃ CH₃ Cl OH Ia1.233NCH₃ H H CH₃ CH₃ Br OH Ia1.234 NCH₃ H H CH₃ CH₃ NO₂ OH Ia1.235 NCH₃ H HCH₃ CH₃ CHF₂ OH Ia1.236 NCH₃ H H CH₃ CH₃ CF₃ OH Ia1.237 NCH₃ H H CH₃ CH₃OCH₃ OH Ia1.238 NCH₃ H H CH₃ CH₃ OCH₂CH₃ OH Ia1.239 NCH₃ H H CH₃ CH₃OCHF₂ OH Ia1.240 NCH₃ H H CH₃ CH₃ OCF₃ OH Ia1.241 NCH₃ CH₃ CH₃ CH₃ HSCH₃ OH Ia1.242 NCH₃ CH₃ CH₃ CH₃ H SCH₂CH₃ OH Ia1.243 NCH₃ CH₃ CH₃ CH₃ HSO₂CH₃ OH Ia1.244 NCH₃ CH₃ CH₃ CH₃ H SO₂CH₂CH₃ OH Ia1.245 NCH₃ CH₃ CH₃CH₃ H SO₂CH(CH₃)₂ OH Ia1.246 NCH₃ CH₃ CH₃ CH₃ H SO₂(CH₂)₂CH₃ OH Ia1.247NCH₃ CH₃ CH₃ CH₃ H Cl OH Ia1.248 NCH₃ CH₃ CH₃ CH₃ H Br OH Ia1.249 NCH₃CH₃ CH₃ CH₃ H NO₂ OH Ia1.250 NCH₃ CH₃ CH₃ CH₃ H CHF₂ OH Ia1.251 NCH₃ CH₃CH₃ CH₃ H CF₃ OH Ia1.252 NCH₃ CH₃ CH₃ CH₃ H OCH₃ OH Ia1.253 NCH₃ CH₃ CH₃CH₃ H OCH₂CH₃ OH Ia1.254 NCH₃ CH₃ CH₃ CH₃ H OCHF₂ OH Ia1.255 NCH₃ CH₃CH₃ CH₃ H OCF₃ OH Ia1.256 NCH₃ CH₃ H CH₃ CH₃ SCH₃ OH Ia1.257 NCH₃ CH₃ HCH₃ CH₃ SCH₂CH₃ OH Ia1.258 NCH₃ CH₃ H CH₃ CH₃ SO₂CH₃ OH Ia1.259 NCH₃ CH₃H CH₃ CH₃ SO₂CH₂CH₃ OH Ia1.260 NCH₃ CH₃ H CH₃ CH₃ SO₂CH(CH₃)₂ OH Ia1.261NCH₃ CH₃ H CH₃ CH₃ SO₂(CH₂)₂CH₃ OH Ia1.262 NCH₃ CH₃ H CH₃ CH₃ Cl OHIa1.263 NCH₃ CH₃ H CH₃ CH₃ Br OH Ia1.264 NCH₃ CH₃ H CH₃ CH₃ NO₂ OHIa1.265 NCH₃ CH₃ H CH₃ CH₃ CHF₂ OH Ia1.266 NCH₃ CH₃ H CH₃ CH₃ CF₃ OHIa1.267 NCH₃ CH₃ H CH₃ CH₃ OCH₃ OH Ia1.268 NCH₃ CH₃ H CH₃ CH₃ OCH₂CH₃ OHIa1.269 NCH₃ CH₃ H CH₃ CH₃ OCHF₂ OH Ia1.270 NCH₃ CH₃ H CH₃ CH₃ OCF₃ OHIa1.271 NCH₃ CH₃ CH₃ CH₃ CH₃ SCH₃ OH Ia1.272 NCH₃ CH₃ CH₃ CH₃ CH₃SCH₂CH₃ OH Ia1.273 NCH₃ CH₃ CH₃ CH₃ CH₃ SO₂CH₃ OH Ia1.274 NCH₃ CH₃ CH₃CH₃ CH₃ SO₂CH₂CH₃ OH Ia1.275 NCH₃ CH₃ CH₃ CH₃ CH₃ SO₂CH(CH₃)₂ OH Ia1.276NCH₃ CH₃ CH₃ CH₃ CH₃ SO₂(CH₂)₂CH₃ OH Ia1.277 NCH₃ CH₃ CH₃ CH₃ CH₃ Cl OHIa1.278 NCH₃ CH₃ CH₃ CH₃ CH₃ Br OH Ia1.279 NCH₃ CH₃ CH₃ CH₃ CH₃ NO₂ OHIa1.280 NCH₃ CH₃ CH₃ CH₃ CH₃ CHF₂ OH Ia1.281 NCH₃ CH₃ CH₃ CH₃ CH₃ CF₃ OHIa1.282 NCH₃ CH₃ CH₃ CH₃ CH₃ OCH₃ OH Ia1.283 NCH₃ CH₃ CH₃ CH₃ CH₃OCH₂CH₃ OH Ia1.284 NCH₃ CH₃ CH₃ CH₃ CH₃ OCHF₂ OH Ia1.285 NCH₃ CH₃ CH₃CH₃ CH₃ OCF₃ OH Ia1.286 NCH₃ CH₂Cl H H H SCH₃ OH Ia1.287 NCH₃ CH₂Cl H HH SCH₂CH₃ OH Ia1.288 NCH₃ CH₂Cl H H H SO₂CH₃ OH Ia1.289 NCH₃ CH₂Cl H H HSO₂CH₂CH₃ OH Ia1.290 NCH₃ CH₂Cl H H H SO₂CH(CH₃)₂ OH Ia1.291 NCH₃ CH₂ClH H H SO₂(CH₂)₂CH₃ OH Ia1.292 NCH₃ CH₂Cl H H H Cl OH Ia1.293 NCH₃ CH₂ClH H H Br OH Ia1.294 NCH₃ CH₂Cl H H H NO₂ OH Ia1.295 NCH₃ CH₂Cl H H HCHF₂ OH Ia1.296 NCH₃ CH₂Cl H H H CF₃ OH Ia1.297 NCH₃ CH₂Cl H H H OCH₃ OHIa1.298 NCH₃ CH₂Cl H H H OCH₂CH₃ OH Ia1.299 NCH₃ CH₂Cl H H H OCHF₂ OHIa1.300 NCH₃ CH₂Cl H H H OCF₃ OH

Extraordinary preference is also given to the compounds of the formulaIa2, in particular to the compounds Ia2.1 to Ia2.300, which differ fromthe corresponding compounds Ia1.1 to Ia1.300 in that R¹¹ is methyl.

Extraordinary preference is also given to the compounds of the formulaIa3, in particular to the compounds Ia3.1 to Ia3.300, which differ fromthe compounds Ia1.1 to Ia1.300 in that R⁸ is ethyl.

Extraordinary preference is also given to the compounds of the formulaIa4, in particular to the compounds Ia4.1 to Ia4.300, which differ fromthe compounds Ia1.1 to Ia1.300 in that R⁸ is ethyl and R¹¹ is methyl.

Extraordinary preference is also given to the compounds of the formulaIa5, in particular to the compounds Ia5.1to Ia5.300, which differ fromthe compounds Ia1.1 to Ia1.300 in that R⁸ is 1-methyl-1-ethyl.

Extraordinary preference is also given to the compounds of the formulaIa6, in particular to the compounds Ia6.1 to Ia6.300, which differ fromthe compounds Ia1.1 to Ia1.300 in that R⁸ is 1-methyl-1-ethyl and R¹¹ ismethyl.

Extraordinary preference is also given to the compounds of the formulaIa7, in particular to the compounds Ia7.1 to Ia7.300, which differ fromthe compounds Ia1.1 to Ia1.300 in that R¹⁰is methyl.

Extraordinary preference is also given to the compounds of the formulaIa8, in particular to the compounds Ia8.1 to Ia8.300, which differ fromthe compounds Ia1.1 to Ia1.300 in that R¹⁰ is methyl and R¹¹ is methyl.

Extraordinary preference is also given to the compounds of the formulaIa9, in particular to the compounds Ia9.1 to Ia9.300, which differ fromthe compounds Ia1.1 to Ia1.300 in that R⁸ and R⁹ are 1-methyl-1-ethyl.

Extraordinary preference is also given to the compounds of the formulaIa10, in particular to the compounds Ia10.1 to Ia10.300, which differfrom the compounds Ia1.1 to Ia1.300 in that R⁸ and R⁹ are1-methyl-1-ethyl and R¹¹ is methyl.

Extraordinary preference is also given to the compounds of the formulaIa11, in particular to the compounds Ia11.1 to Ia.11.300, which differfrom the compounds Ia1.1 to Ia1.300 in that R⁸ is ethyl and R¹⁰ ismethyl.

Extraordinary preference is also given to the compounds of the formulaIa12, in particular to the compounds Ia12.1 to Ia12.300, which differfrom the compounds Ia1.1 to Ia1.300 in that R⁸ is ethyl and R¹⁰ and R¹¹are methyl.

The 3-(heterocyclyl)-substituted benzoylpyrazoles of the formula I canbe obtained by various routes, for example by the processes below.

Process A:

Reaction of pyrazoles of the formula II with an activated benzoic acidIIIα or a benzoic acid IIIβ, which is preferably activated in situ, togive the corresponding acylation product IV, followed by rearrangement,gives compounds of the formula I where R⁷=OH.

L¹ is a nucleophilically replaceable leaving group, such as halogen, forexample bromine, chlorine, hetaryl, for example imidazolyl, pyridyl,carboxylate, for example acetate, trifluoroacetate etc.

The activated benzoic acid can be employed directly, such as in the caseof the benzoyl halides, or be generated in situ, for example usingdicyclohexylcarbodiimide, triphenylphosphine/azodicarboxylic ester,2-pyridine disulfide/triphenylphosphine, carbonyldiimidazole, etc.

It may be advantageous to carry out the acylation reaction in thepresence of a base. The reactants and the auxiliary base areadvantageously employed in equimolar amounts. A slight excess ofauxiliary base, for example from 1.2 to 1.5 molar equivalents, based onII, may be advantageous in certain cases.

Suitable auxiliary bases are tertiary alkylamines, pyridine or alkalimetal carbonates. Suitable for use as solvents are, for example,chlorinated hydrocarbons, such as methylene chloride,1,2-dichloroethane, aromatic hydrocarbons, such as toluene, xylene,chlorobenzene, ethers, such as diethyl ether, methyl tert-butyl ether,dimethoxyethane, tetrahydrofuran, dioxane, polar aprotic solvents, suchas acetonitrile, dimethylformamide, dimethyl sulfoxide, or esters, suchas ethyl acetate, or mixtures of these.

If the activated carboxylic acid component used is a benzoyl halide, itmay be advantageous to cool the reaction mixture to 0-10° C. when addingthis reaction partner. The mixture is subsequently stirred at 20-100°C., preferably at 25-50° C., until the reaction has ended. Work-up iscarried out in a customary manner, for example by pouring the reactionmixture into water and extracting the product of value. Solvents whichare particularly suitable for this purpose are methylene chloride,diethyl ether, dimethoxyethane and ethyl acetate. The organic phase isdried and the solvent is removed, after which the crude ester can beemployed for the rearrangement without any further purification.

The rearrangement of the esters to the compounds of the formula I isadvantageously carried out at 20 -40° C in a solvent and in the presenceof a base and, if appropriate, using a cyano compound as catalyst.

Suitable solvents are, for example, acetonitrile, methylene chloride,1,2-dichloroethane, dioxane, ethyl acetate, dimethoxyethane, toluene ormixtures of these. Preferred solvents are acetonitrile and dioxane.

Suitable bases are tertiary amines, such as triethylamine or pyridine,or alkali metal carbonates, such as sodium carbonate or potassiumcarbonate, which are preferably employed in an equimolar amount or an upto four-fold excess, based on the ester. Preference is given to usingtriethylamine or alkali metal carbonates, preferably in twice theequimolar amount, based on the ester.

Suitable cyano compounds are inorganic cyanides, such as sodium cyanideand potassium cyanide, and organic cyano compounds, such asacetonecyanohydrine and trimethylsilyl cyanide. They are employed in anamount of from 1 to 50 mol percent, based on the ester. Preference isgiven to using acetonecyanohydrine or trimethylsilyl cyanide, forexample in an amount of from 5 to 15, preferably 10, mol percent, basedon the ester.

Work-up can be carried out in the manner known per se. The reactionmixture is, for example, acidified with dilute mineral acid, such as 5%strength hydrochloric acid or sulfuric acid, and extracted with anorganic solvent, for example methylene chloride or ethyl acetate. Theorganic extract can be extracted with 5-10% strength alkali metalcarbonate solution, for example sodium carbonate or potassium carbonatesolution. The aqueous phase is acidified and the resulting precipitateis filtered off with suction and/or extracted with methylene chloride orethyl acetate, and the mixture is dried and concentrated. (Examples forthe preparation of esters of hydroxypyrazoles and for the rearrangementof the esters are given, for example, in EP-A 282 944 and U.S. Pat No.4,643,757).

However, it is also possible to generate the “acylation product” IV insitu by reacting a pyrazole of the formula II, or an alkali metal saltthereof, with a 3-(heterocyclyl)benzene derivative of the formula V inthe presence of carbon monoxide, a catalyst and a base.

L² is a leaving group, such as halogen, for example chlorine, bromine oriodine, or sulfonate, such as mesylate or triflate; preference is givento bromine or triflate.

The “acylation product” IV proceeds to react, directly or indirectly, togive the 3-(heterocyclyl)-substituted benzoylpyrazole of the formula I.

Suitable catalysts are palladium-ligand complexes in which the palladiumis present in oxidation state 0, metallic palladium, which hasoptionally been absorbed on a carrier, and preferably palladium(II)salts. The reaction with palladium(II) salts and metallic palladium ispreferably carried out in the presence of complex ligands.

An example of a suitable palladium(0)-ligand complex istetrakis(triphenylphosphine)palladium.

Metallic palladium is preferably absorbed on an inert carrier such as,for example, activated carbon, silica, alumina, barium sulfate orcalcium carbonate. The reaction is preferably carried out in thepresence of complex ligands such as, for example, triphenylphosphine.

Examples of suitable palladium(II) salts are palladium acetate andpalladium chloride. The presence of complex ligands such as, forexample, triphenylphosphine is preferred.

Suitable complex ligands for the palladium-ligand complexes, or in whosepresence the reaction is preferably carried out with metallic palladiumor palladium(II) salts, are tertiary phosphines whose structure isrepresented by the following formulae:

where z is 1 to 4 and the radicals R^(a) to R^(g) are C₁-C₆-alkyl,C₃-C₆-cycloalkyl, aryl-C₁-C2-alkyl or, preferably, aryl. Aryl is, forexample, naphthyl and unsubstituted or substituted phenyl such as, forexample, 2-tolyl and, in particular, unsubstituted phenyl.

The complex palladium salts can be prepared in a manner known per sestarting from commercially available palladium salts such as palladiumchloride or palladium acetate and the appropriate phosphines such as,for example, triphenylphosphine or 1,2-bis(diphenylphosphino)ethane.Many of the complexed palladium salts are also commercially available.Preferred palladium salts are [(R)(+)2,2′,-bis(diphenylphosphino)-1,1′-binaphthyl]-palladium(II) chloride,bis(triphenylphosphine)palladium(II) acetate and, in particular,bis(triphenylphosphine)palladium(II) chloride.

The palladium catalyst is usually employed in a concentration of from0.05 to 5 mol %, and preferably 1-3 mol %.

Suitable bases are tertiary amines, such as, for example,N-methylpiperidine, ethyldiisopropylamine,1,8-bisdimethylaminonaphthalene or, in particular, triethylamine. Alsosuitable are alkali metal carbonates, such as sodium carbonate orpotassium carbonate. However, mixtures of potassium carbonate andtriethylamine are also suitable.

In general, from 2 to 4 molar equivalent, in particular 2 molarequivalents, of the alkali metal carbonate, and from 1 to 4 molarequivalents, in particular 2 molar equivalents, of the tertiary amineare employed, based on the 3-(heterocylyl)-benzene derivatives of theformula V.

Suitable solvents are nitriles, such as benzonitrile and acetonitrile,amides, such as dimethylformamide, dimethylacetamide,tetra-C₁-C₄-alkylureas or N-methylpyrrolidone and, preferably, ethers,such as tetrahydrofuran and methyl tert-butyl ethers. Particularpreference is given to ethers, such as 1,4-dioxane and dimethoxyethane.

Process B:

Compounds of the formula I where R⁷ ≠hydroxyl are obtained by reactingcompounds of the formula I where R⁷=hydroxyl with alkylating agents,sulfonylating agents or acylating agents L³-R^(7a) (VI).

L³ is a nucleophilically replaceable leaving group, such as halogen, forexample bromine or chlorine, acyloxy, for example acetyloxy orethylcarbonyloxy, or alkylsulfonyloxy, for example methylsulfonyloxy ortrifluoromethylsulfonyloxy.

R^(7a) is C₁-C₆-alkyl, C₃-C₆-alkenyl, C₁-C₆-alkylsulfonyl,C₁₋C₆-alkylcarbonyl, C₁-C₄-(alkylthio)carbonyl, phenylsulfonyl orphenylcarbonyl, where the phenyl radical of the two last-mentionedsubstituents may be partially or fully halogenated and/or may carry oneto three of the following groups: nitro, cyano, C₁-C₄-alkyl,C₁-C₄-haloalkyl, C₁-C₄-alkoxy or C₁-C₄-haloalkoxy.

The compounds of the formula VI can be employed directly, such as, forexample, in the case of the sulfonyl halides or sulfonic anhydrides, orbe generated in situ, for example activated sulfonic acids (usingsulfonic acid and dicyclohexylcarbonyldiimide, carbonyldiimidazole,etc.).

The starting materials are generally employed in equimolar amounts.However, it may also be advantageous to employ an excess of one or theother component.

If appropriate, it may be advantageous to carry out the reaction in thepresence of a base. The reactants and the auxiliary base areadvantageously employed in equimolar amounts. An excess of auxiliarybase, for example from 1.5 to 3 molar equivalents, based on I, may beadvantageous in certain cases.

Suitable auxiliary bases are tertiary alkylamines, such astriethylamine, pyridine, alkali metal carbonates, for example sodiumcarbonate or potassium carbonate, and alkali metal hydrides, for examplesodium hydride. Preference is given to using triethylamine and pyridine.

Suitable solvents are, for example, chlorinated hydrocarbons, such asmethylene chloride and 1,2-dichloroethane, aromatic hydrocarbons, forexample toluene, xylene, chlorobenzene, ethers, such as diethyl ether,methyl tert-butyl ether, tetrahydrofuran and dioxane, polar aproticsolvents, such as acetonitrile, dimethylformamide, dimethyl sulfoxide,or esters, such as ethyl acetate, or mixtures of these.

In general, the reaction temperature is in the range from 0° C. to theboiling point of the reaction mixture.

Work-up can be carried out in the manner known per se to give theproduct.

The pyrazoles of the formula II used as starting materials are known orcan be prepared by the process known per se (for example EP-A 240 001and J. Prakt. Chem. 315, 383 (1973)).

The activated benzoic acids IIIα can be obtained in a manner known perse from the benzoic acids IIIβ. The latter for their part are obtainedby hydrolysis from the corresponding esters VII. These can be preparedby converting an oxime or hydrazone of the formula VIII into thecorresponding hydroxamic acid halide, in particular hydroxamic acidchloride, or carbohydrazide halide, in particular carbohydrazidechloride; generating a nitrile oxide or nitrile imine in situ andreacting this with an alkene (cf., for example, Chem. Ber. 106,3258-3274 (1973)).

L⁴ denotes a C₁-C₆-alkoxy radical.

However, the benzoic acids IIIβ can also be obtained by converting anoxime or hydrazine of the formula IX into the corresponding nitrileoxides or nitrile imines and reacting these with alkenes to give thecorresponding cycloaddition products (cf., for example, Chem. Ber. 106,3258-3274 (1973)). Thus, for example, the oxime of the formula IX (X═O)is oxidized with sodium hypochlorite and reacted with a suitable alkenein an inert solvent such as methylene chloride, chloroform,tetrahydrofuran, dioxane or acetonitrile. The product is then convertedin the presence of a catalyst and a base into the benzoic acid IIIβusing carbon monoxide and water.

L² denotes a leaving group, such as halogen, for example chlorine,bromine or iodine, or sulfonate, such as mesylate or triflate,preferably bromine or triflate.

With respect to the carbonylation reaction, what has been said aboveapplies analogously.

The compounds of the formulae III and V are in each case novel as such

where in each case the variables R¹, R³ to R⁶ and X are as defined underthe compounds of the formula I and

R² is C₁-C₄-haloalkyl;

L is hydroxyl or a radical that can be removed by hydrolysis; or

L² is a leaving group that can be displaced nucleophilically.

Examples of radicals that can be removed by hydrolysis are alkoxy,phenoxy, alkylthio and phenylthio radicals, which may be unsubstitutedor substituted, halides, hetaryl radicals attached via nitrogen, aminoand imino radicals, which may be unsubstituted or substituted, etc.

Examples of nucleophilically displaceable leaving groups are halogen,C₁-C₄-alkylsulfonyloxy and C₁-C₄-haloalkylsulfonyloxy;

Preferred compounds of the formula III are those compounds in which L ishalogen, in particular chlorine or bromine.

Preference is also given to those compounds of the formula III in whichL is C₁-C₆-alkoxy.

Preference is also given to those compounds of the formula III in whichL is hydroxyl.

With respect to the variables X, R¹ and R³ to R⁶, the particularlypreferred embodiments of the compounds of the formulae III and Vcorrespond to those of the compounds of the formula I.

PREPARATION EXAMPLES4-[2-Methyl-3-(4,5-dihydroisoxazol-3-yl)-4-methylsulfonylbenzoyl)]-5-hydroxy-1-(1,1-dimethyl-1-ethyl)-1H-pyrazole

(Compound 2.1)

Variant 1:

0.61 g (3.5 mmol) of 1-(1,1-dimethyl-1-ethyl)-5-hydroxy-1H-pyrazole and0.79 g (3.9 mmol) of dicyclohexylcarbodiimide were added to a solutionof 1.0 g (3.5 mmol) of2-methyl-3-(4,5-dihydroisoxazol-3-yl)-4-methylsulfonylbenzoic acid indioxane, and the mixture was stirred at room temperature for 12 hours.Insoluble components were separated off, and 0.58 g (4.2 mmol) ofpotassium carbonate was then added and the mixture was refluxed for 3hours. The solvent was then distilled off, the residue was taken up in5% strength potassium carbonate solution and washed with methylenechloride and toluene, the pH was adjusted to 3 using 10% strengthhydrochloric acid and the mixture was extracted with methylene chloride.This methylene chloride solution was dried and the solvent was removed.This gave 0.81 g (57% of theory) of4-[2-methyl-3-(4,5-dihydroisoxazol-3-yl)-4-methylsulfonylbenzoyll-5-hydroxy-1-(1,1-dimethyl-1-ethyl)-1H-pyrazole]M.p. 195-198° C.

Variant 2

3.78 g (32 mmol) of thionyl chloride were added to a solution of 6 g(21.2 mmol) of2-methyl-3-(4,5-dihydroisoxazol-3-yl)-4-methylsulfonylbenzoic acid intoluene, and the mixture was refluxed for 4 hours. The solvent wasremoved, the residue was then taken up in dimethoxyethane and a solutionof 2.97 g (21.2 mmol) of 1-(l, 1-dimethyl-1-ethyl)-5-hydroxy-1H-pyrazolein dimethoxyethane was added dropwise. The mixture was subsequentlystirred at room temperature for 12 hours and refluxed for 3.5 hours. Thereaction mixture was cooled, the solvent was distilled off, and theresidue was taken up in 5% strength potassium carbonate solution andwashed with methylene chloride. The resulting aqueous phase was adjustedto pH=1 using hydrochloric acid, and the resulting precipitate wasfiltered off with suction. This gave 4.89 g (52%) of4-[2-methyl-3-(4,5-dihydroisoxazol-3-yl)-4-methylsulfonylbenzoyll-5-hydroxy-1-(1,1-dimethyl-1-ethyl)-1H-pyrazole]M.p. 195-198° C.

In addition to the compound above, Table 2 lists further3-(heterocyclyl)-substituted benzoylpyrazoles of the formula I whichwere prepared or are preparable in a similar manner.

TABLE 2

I where X = O physical data m.p. [° C.] ¹H—NMR No. R¹ R² R³ R⁴ R⁵ R⁶ R⁷R⁸ R⁹ R¹⁰ R¹¹ [δ in ppm] 2.1 CH₃ H H H H SO₂CH₃ OH CH₃ CH₃ CH₃ H 195-1982.2 CH₃ H H H H SO₂CH₃ OCH(CH₃)₂ CH₃ CH₃ CH₃ H oil 2.3 CH₃ H H H HSO₂CH₃ OCO[3-F—C₆H₄] CH₃ CH₃ CH₃ H 210-211 2.4 CH₃ H H H H SO₂CH₃OCO[3,5-(CF₃)₂—C₆H₃] CH₃ CH₃ CH₃ H oil 2.5 CH₃ H H H H SO₂CH₃OCO[2,4-F₂—C₆H₃] CH₃ CH₃ CH₃ H 145-148 2.6 CH₃ H H H H SO₂CH₃OCO[3,5-F₂—C₆H₃] CH₃ CH₃ CH₃ H 100-105 2.7 CH₃ H H H H SO₂CH₃OCO[3-(CF₃)—C₆H₄] CH₃ CH₃ CH₃ H 90-93 2.8 CH₃ H H H H SO₂CH₃ OH CH₃ CH₃CH₃ CH₃ 198-200 2.9 CH₃ H H H H SO₂CH₃ OH CH₃ CH₃ H H 203-205 2.10CH₂—CH₃ H H H H SO₂CH₃ OH CH₃ CH₃ CH₃ H 75-80 2.11 CH₃ H H H H SO₂CH₃ OHCH(CH₃)₂ CH₃ H H 90-95 2.12 CH₃ H H H H SO₂CH₃ OCOC₆H₅ CH(CH₃)₂ CH₃ H H 95-100 2.13 CH₃ CH₂Cl H H H SO₂CH₃ OH CH₃ CH₃ CH₃ H 80-81 2.14 CH₃CH₂Cl H H H SO₂CH₃ OH CH₃ CH₃ H H 75-84 2.15 CH₃ CH₂Cl H H H SO₂CH₃OCO[3-F—C₆H₄] CH₃ CH₃ H H 77-83 2.16 CH₃ H H H H SO₂CH₃ OH CH(CH₃)₂CH(CH₃)₂ H H 120-125 2.17 CH₃ CH₂Cl CH₂Cl H H SO₂CH₃ OH CH₃ CH₃ H H73-79 2.18 CH₃ CH₂Cl CH₂Cl H H SO₂CH₃ OH CH₃ CH₃ CH₃ H 73-78 2.19 CH₃ HH H H SO₂CH₃ OCH₃ CH₃ CH₃ H H oil 2.20 CH₃ H H H H SO₂CH₃ OCH₂CH₃ CH₃CH₃ H H 165-170 2.21 CH₃ H H H H SO₂CH₃ OCH(CH₃)₂ CH₃ CH₃ H H oil 2.22CH₃ H H H H SO₂CH₃ OCOC₆H₅ CH₃ CH₃ H H oil 2.23 CH₃ H H H H SO₂CH₃OCO[3-F—C₆H₄] CH₃ CH₃ H H 110-115 2.24 CH₃ H H H H SO₂CH₃ OCOCH₃ CH₃ CH₃H H 80-85 2.25 CH₃ H H H H SO₂CH₃ OSO₂[4-CH₃—C₆H₄] CH₃ CH₃ H H  95-1002.26 CH₃ H H H H SO₂CH₃ OCOSCH₃ CH₃ CH₃ H H 143-145 2.27 CH₃ H H H HSO₂CH₃ OCOC₆H₅ CH₃ CH₃ CH₃ H 228-230

The 3-(heterocyclyl)-substituted benzoylpyrazoles of the formula I andtheir agriculturally useful salts are suitable, both in the form ofisomer mixtures and in the form of the pure isomers, as herbicides. Theherbicidal compositions comprising compounds of the formula I controlvegetation on non-crop areas very efficiently, especially at high ratesof application. They act against weeds and harmful grasses in crops suchas wheat, rice, maize, soya and cotton without causing any significantdamage to the crop plants. This effect is mainly observed at low ratesof application.

Depending on the particular application method used, the compounds ofthe formula I, or the herbicidal compositions comprising them, canadditionally be employed in a further number of crop plants foreliminating undesirable plants. Examples of suitable crops are thefollowing:

Allium cepa, Ananas comosus, Arachis hypogaea, Asparagus officinalis,Beta vulgaris spec. altissima, Beta vulgaris spec. rapa, Brassica napusvar. napus, Brassica napus var. napobrassica, Brassica rapa var.silvestris, Camellia sinensis, Carthamus tinctorius, Caryaillinoinensis, Citrus limon, Citrus sinensis, Coffea arabica (Coffeacanephora, Coffea liberica), Cucumis sativus, cynodon dactylon, Daucuscarota, Elaeis guineensis, Fragaria vesca, Glycine max, Gossypiumhirsutum, (Gossypium arboreum, Gossypium herbaceum, Gossypiumvitifolium), Helianthus annuus, Hevea brasiliensis, Hordeum vulgare,Humulus lupulus, Ipomoea batatas, Juglans regia, Lens culinaris, Linumusitatissimum, Lycopersicon lycopersicum, Malus spec., Manihotesculenta, Medicago sativa, Musa spec., Nicotiana tabacum (N. rustica),Olea europaea, Oryza sativa, Phaseolus lunatus, Phaseolus vulgaris,Picea abies, Pinus spec., Pisum sativum, Prunus avium, Prunus persica,Pyrus communis, Ribes sylvestre, Ricinus communis, Saccharumofficinarum, Secale cereale, Solanum tuberosum, Sorghum bicolor (s.vulgare), Theobroma cacao, Trifolium pratense, Triticum aestivum,Triticum durum, Vicia faba, Vitis vinifera and Zea mays.

In addition, the compounds of the formula I may also be used in cropswhich tolerate the action of herbicides owing to breeding, includinggenetic engineering methods.

The compounds of the formula I, or the herbicidal compositionscomprising them, can be used for example in the form of ready-to-sprayaqueous solutions, powders, suspensions, also highly-concentratedaqueous, oily or other suspensions or dispersions, emulsions, oildispersions, pastes, dusts, materials for broadcasting, or granules, bymeans of spraying, atomizing, dusting, broadcasting or watering. The useforms depend on the intended aims; in any case, they should guarantee avery fine distribution of the active compounds according to theinvention.

The herbicidal compositions comprise a herbicidally effective amount ofat least one compound of the formula I or an agriculturally useful saltof I and auxiliaries which are customarily used for formulating cropprotection agents.

Essentially, suitable inert auxiliaries include: mineral oil fractionsof medium to high boiling point, such as kerosene and diesel oil,furthermore coal tar oils and oils of vegetable or animal origin,aliphatic, cyclic and aromatic hydrocarbons, eg. paraffins,tetrahydronaphthalene, alkylated naphthalenes and their derivatives,alkylated benzenes and their derivatives, alcohols such as methanol,ethanol, propanol, butanol and cyclohexanol, ketones such ascyclohexanone, or strongly polar solvents, e.g. amines such asN-methylpyrrolidone, and water.

Aqueous use forms can be prepared from emulsion concentrates,suspensions, pastes, wettable powders or water-dispersible granules byadding water. To prepare emulsions, pastes or oil dispersions, thesubstances, either as such or dissolved in an oil or solvent, can behomogenized in water by means of a wetting agent, tackifier, dispersantor emulsifier. Alternatively, it is possible to prepare concentratescomprising active compound, wetting agent, tackifier, dispersant oremulsifier and, if desired, solvent or oil, which are suitable fordilution with water.

Suitable surfactants (adjuvants) are the alkali metal salts, alkalineearth metal salts and ammonium salts of aromatic sulfonic acids, eg.ligno-, phenol-, naphthalene- and dibutylnaphthalenesulfonic acid, andof fatty acids, alkyl- and alkylarylsulfonates, alkyl sulfates, laurylether sulfates and fatty alcohol sulfates, and salts of sulfated hexa-,hepta- and octadecanols, and also of fatty alcohol glycol ether,condensates of sulfonated naphthalene and its derivatives withformaldehyde, condensates of naphthalene, or of the naphthalenesulfonicacids with phenol and formaldehyde, polyoxyethylene octylphenol ether,ethoxylated isooctyl-, octyl- or nonylphenol, alkylphenyl ortributylphenyl polyglycol ether, alkylaryl polyether alcohols,isotridecyl alcohol, fatty alcohol/ethylene oxide condensates,ethoxylated castor oil, polyoxyethylene alkyl ethers or polyoxypropylenealkyl ethers, lauryl alcohol polyglycol ether acetate, sorbitol esters,lignin-sulfite waste liquors or methylcellulose.

Powders, materials for broadcasting and dusts can be prepared by mixingor grinding the active compounds together with a solid carrier.

Granules, e.g. coated granules, impregnated granules and homogeneousgranules, can be prepared by binding the active compounds to solidcarriers. Solid carriers are mineral earths, such as silicas, silicagels, silicates, talc, kaolin, limestone, lime, chalk, bole, loess,clay, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate,magnesium oxide, ground synthetic materials, fertilizers such asammonium sulfate, ammonium phosphate and ammonium nitrate, ureas, andproducts of vegetable origin, such as cereal meal, tree bark meal, woodmeal and nutshell meal, cellulose powders, or other solid carriers.

The concentrations of the compounds of the formula I in the ready-to-usepreparations can be varied within wide ranges. In general, theformulations comprise about from 0.001 to 98% by weight, preferably 0.01to 95% by weight, of at least one active compound. The active compoundsare employed in a purity of from 90% to 100%, preferably 95% to 100%(according to the NMR spectrum).

The following formulation examples illustrate the preparation of suchformulations:

I. 20 parts by weight of the compound No. 2.8 are dissolved in a mixturecomposed of 80 parts by weight of alkylated benzene, 10 parts by weightof the adduct of 8 to 10 mol of ethylene oxide to 1 mol of oleic acidN-monoethanolamide, 5 parts by weight of calcium dodecylbenzenesulfonateand 5 parts by weight of the adduct of 40 mol of ethylene oxide to 1 molof castor oil. Pouring the solution into 100,000 parts by weight ofwater and finely distributing it therein gives an aqueous dispersionwhich comprises 0.02% by weight of the active compound.

II. 20 parts by weight of the compound No. 2.9 are dissolved in amixture composed of 40 parts by weight of cyclohexanone, parts by weightof isobutanol, 20 parts by weight of the adduct of 7 mol of ethyleneoxide to 1 mol of isooctylphenol and 10 parts by weight of the adduct of40 mol of ethylene oxide to 1 mol of castor oil. Pouring the solutioninto 100,000 parts by weight of water and finely distributing it thereingives an aqueous dispersion which comprises 0.02% by weight of theactive compound.

III. 20 parts by weight of the active compound No. 2.3 are dissolved ina mixture composed of 25 parts by weight of cyclohexanone, 65 parts byweight of a mineral oil fraction of boiling point 210 to 280° C. and 10parts by weight of the adduct of 40 mol of ethylene oxide to 1 mol ofcastor oil. Pouring the solution into 100,000 parts by weight of waterand finely distributing it therein gives an aqueous dispersion whichcomprises 0.02% by weight of the active compound.

IV. 20 parts by weight of the active compound No. 2.3 are mixedthoroughly with 3 parts by weight of sodiumdiisobutylnaphthalenesulfonate, 17 parts by weight of the sodium salt ofa lignosulfonic acid from a sulfite waste liquor and 60 parts by weightof pulverulent silica gel, and the mixture is ground in a hammer mill.Finely distributing the mixture in 20,000 parts by weight of water givesa spray mixture which comprises 0.1% by weight of the active compound.

V. 3 parts by weight of the active compound No. 2.9 are mixed with 97parts by weight of finely divided kaolin. This gives a dust whichcomprises 3% by weight of the active compound.

VI. 20 parts by weight of the active compound No. 2.8 are mixedintimately with 2 parts by weight of calcium dodecylbenzenesulfonate, 8parts by weight of fatty alcohol polyglycol ether, 2 parts by weight ofthe sodium salt of a phenol/urea/formaldehyde condensate and 68 parts byweight of a paraffinic mineral oil. This gives a stable oily dispersion.

VII. 1 part by weight of the active compound No. 2.3 is dissolved in amixture composed of 70 parts by weight of cyclohexanone, 20 parts byweight of ethoxylated isooctylphenol and 10 parts by weight ofethoxylated castor oil. This gives a stable emulsion concentrate.

VIII. 1 part by weight of the active compound No. 2.9 is dissolved in amixture composed of 80 parts by weight of cyclohexanone and 20 parts byweight of Wettol® EM 31 (=nonionic emulsifier based on ethoxylatedcastor oil).

This gives a stable emulsion concentrate.

The compounds of the formula I or the herbicidal compositions can beapplied pre- or post-emergence. If the active compounds are less welltolerated by certain crop plants, application techniques may be used inwhich the herbicidal compositions are sprayed, with the aid of thespraying equipment, in such a way that they come into contact as littleas possible, if at all, with the leaves of the sensitive crop plants,while the active compounds reach the leaves of undesirable plantsgrowing underneath, or the bare soil surface (post-directed, lay-by).

The application rates of the compound of the formula I are from 0.001 to3.0, preferably 0.01 to 1.0, kg/ha of active substance (a.s.), dependingon the control target, the season, the target plants and the growthstage.

To widen the activity spectrum and to achieve synergistic effects, the3-(heterocyclyl)-substituted benzoylpyrazoles of the formula I may bemixed with a large number of representatives of other herbicidal orgrowth-regulating active compound groups and then applied concomitantly.Suitable components for mixtures are, for example, 1,2,4-thiadiazoles,1,3,4-thiadiazoles, amides, aminophosphoric acid and its derivatives,aminotriazoles, anilides, (het)aryloxyalkanoic acids and theirderivatives, benzoic acid and its derivatives, benzothiadiazinones,2-(het)aroyl-1,3-cyclohexanediones, hetaryl aryl ketones,benzylisoxazolidinones, meta-CF₃-phenyl derivatives, carbamates,quinolinecarboxylic acid and its derivatives, chloroacetanilides,cyclohexeneone oxime ether derivatives, diazines, dichloropropionic acidand its derivatives, dihydrobenzofurans, dihydrofuran- 3-ones,dinitroanilines, dinitrophenols, diphenyl ethers, dipyridyls,halocarboxylic acids and their derivatives, ureas, 3-phenyluracils,imidazoles, imidazolinones, N-phenyl-3,4,5,6-tetrahydrophthalimides,oxadiazoles, oxiranes, phenols, aryloxy- and hetaryloxyphenoxypropionicesters, phenylacetic acid and its derivatives, 2-phenylpropionic acidand its derivatives, pyrazoles, phenylpyrazoles, pyridazines,pyridinecarboxylic acid and its derivatives, 2-pyrimidyl ethers,sulfonamides, sulfonylureas, triazines, triazinones, triazolinones,triazolecarboxamides and uracils.

It may furthermore be advantageous to apply the compounds of the formulaI, alone or else concomitantly in combination with other herbicides, inthe form of a mixture with other crop protection agents, for exampletogether with agents for controlling pests or phytopathogenic fungi orbacteria. Also of interest is the miscibility with mineral saltsolutions, which are employed for treating nutritional and trace elementdeficiencies. Non-phytotoxic oils and oil concentrates may also beadded.

USE EXAMPLES

The herbicidal activity of the 3-(heterocyclyl)-substitutedbenzoylpyrazoles of the formula I was demonstrated by the followinggreenhouse experiments:

The culture containers used were plastic flowerpots containing loamysand with approximately 3.0% of humus as the substrate. The seeds of thetest plants were sown separately for each species.

For the pre-emergence treatment, the active compounds, which had beensuspended or emulsified in water, were applied directly after sowing bymeans of finely distributing nozzles. The containers were irrigatedgently to promote germination and growth and subsequently covered withtransparent plastic hoods until the plants had rooted. This cover causesuniform germination of the test plants, unless this has been adverselyeffected by the active compounds.

For the post-emergence treatment, the test plants were first grown to aheight of 3 to 15 cm, depending on the plant habit, and only thentreated with the active compounds which had been suspended or emulsifiedin water. The test plants were, for this purpose, either sown directlyand grown in the same containers, or they were first grown separately asseedlings and transplanted into the test containers a few days prior totreatment. The application rate for the post-emergence treatment was0.5, 0.25, 0.125 or 0.0625 kg of a.s. (active substance)/ha.

Depending on the species, the plants were kept at 10-25° C. or 20-35° C.The test period extended over 2 to 4 weeks. During this time, the plantswere tended, and their response to the individual treatments wasevaluated.

The evaluation was carried out using a scale from 0 to 100. 100 means noemergence of the plants, or complete destruction of at least the aerialparts and 0 means no damage, or normal course of growth.

The plants used in the greenhouse experiments were of the followingspecies:

Scientific name Common name Abutilon theophrasti velvet leaf Amaranthusretroflexus pigweed Avena fatua wild oat Chenopodium albumlamb's-quarters Echinochloa crus galli barnyard grass Polygonumpersicaria lady's-thumb Setaria faberi giant foxtail Setaria viridisgreen foxtail Sinapis alba white mustard Solanum nigrum black nightshade

At application rates of 0.125 or 0.0625 kg/ha, the compound 2.3 (Table2) showed very good action against the undesirable plants barnyardgrass, pigweed, lamb's-quarters, lady's-thumb and black nightshade whenused in the post-emergence method.

Furthermore, compound 2.8 (Table 2) effected very good post-emergencecontrol at application rates of 0.5 or 0.25 kg/ha of the harmful plantsbarnyard grass, green foxtail, lamb's-quarters and black nightshade.

The action of compound 2.9 (Table 2), when applied in the post-emergencemethod at application rates of 0.25 or 0.125 kg/ha, on the grasses wildoat and green foxtail and on the weeds pigweed, lady's-thumb and whitemustard is very good.

Likewise, the compound 2.10 (Table 2) effects, at application rates of0.25 or 0.125 kg/ha, very good post-emergence control of the undesirableplants barnyard grass, lamb's-quarters, white mustard and blacknightshade.

We claim:
 1. A 3-(heterocyclyl)-substituted benzoylpyrazole of theformula I

where: X is O, NH or N(C₁-C₆-alkyl); R¹ is C₁-C6-alkyl; R², R³, R⁴, R⁵are hydrogen, C₁-C₄-alkyl or C₁-C₄-haloalkyl; R⁶ is halogen, nitro,C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C4-haloalkoxy, C₁-C₄-alkylthio,C₁-C₄-haloalkylthio, C₁-C₄-alkylsulfonyl or C₁-C₄-haloalkyloulfonyl; R⁷is hydroxyl, C₁-C₆-alkoxy, C₃-C₆-alkenyloxy, C₁-C₆-alkylsulfonyloxy,C₁-C6-alkylcarbonyloxy, C-C₄-(alkylthio)carbonyloxy, phenylsultonyloxyor phenylcarbonyloxy, where the phenyl radical of the two last-mentionedsubstituents may be partially or fully halogenated and/or may carry oneto three of the following groups: nitro, cyano, C₁-C4-alkyl,C₁-C₄-haloalkyl, C₁-C₄-alkoxy or C₁-C₄-haloalkoxy; R⁸, R⁹ areC₁-C₄-alkyl; R¹⁰ is hydrogen or C₁-C₄-alkyl; where the number of thecarbon atoms of the radicals R⁸, R⁹ and R¹⁰ together is at most 7, R¹¹is hydrogen or C₁-C₄-alkyl; and its agriculturally useful salts.
 2. A3-(heterocyclyl)-substituted benzoylpyrazole of the formula I as claimedin claim 1 where X is O; R¹ is C₂-C₄-alkyl; R⁶ is C₁-C₄-alkylthio orC₁-C₄-alkylsulfonyl.
 3. A 3-(heterocyclyl)-substituted benzoylpyrazoleof the formula I as claimed in claim 1 where X is O; R¹ is C₁-C₄-alkyl;R⁶ is halogen nitro, C₁-C₄haloalkyl, C₁-C₄-alkoxy or C₁-C₄-haloalkoxy.4. A 3-(heterocyclyl)-substituted benzoylpyrazole of the formula I asclaimed in claim 1 where X is N(C₁-C₆-alkyl).
 5. A process for preparing3-(heterocyclyl)-substituted benzoylpyrazoles of the formula I asclaimed in claim 1, which comprises acylating a pyrazole of the formulaII

with an activated benzoic acid IIIα or a benzoic acid IIIβ,

where the variables X, R¹ to R⁶ and R⁸ to R¹¹ are as defined in claim 1and L¹ is a nucleophilically replaceable leaving group and rearrangingthe acylation product, in the presence or absence of a catalyst, to givethe compounds of the formula I where R⁷is a hydroxyl and optionally, toprepare 3-(heterocyclyl)-substituted benzoylpyrazoles of formula I whereR⁷ is not hydroxyl as claimed in claim 1, reacting the obtained productwith a compound of formula VI L³—R^(7a)  VI wherein L³ is anucleophilically replaceable leaving group, and R^(7a) is C₁-C₆-alkyl,C₃-C₆-alkenyl, C₁-C₆-alkylsulfonyl, C₁-C₆-alkylcarbonyl,C₁-C₄-(alkylthio)carbanyloxy, phenylsulfonyl or phenylcarbonyl, wherethe phenyl radical of the two last-mentioned substituents may bepartially of fully halogenated and/or may carry one to three of thefollowing groups; nitro, cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl,C₁-C₄-alkoxy or C₁-C₄-haloalkoxy.
 6. A process for preparing3-(heterocyclyl)-substituted benzoylpyrazoles of the formula I asclaimed in claim 1, which comprises reacting a pyrazole of the formulaII

in which the variables R⁸ to R¹¹ are as defined in claim 1, or an alkalimetal salt thereof, with a 3-(heterocyclyl)benzene derivative of theformula V

where the variables X and R¹ to R⁶ are as defined in claim 1 and L² is aleaving group in the presence of carbon monoxide, a catalyst and a base,to give the compounds of formula I where R⁷ is an hydroxyl andoptionally, to prepare 3-(heterocyclyl)-substituted benzylpyrazoles offormula I were R⁷ is not hydroxyl as claimed in claim 1, reacting theobtained product with a compound of formula VI L³—R^(7a)  VI wherein L³is a nucleophilically replaceable leaving group, and R^(7a) isC₁-C₆-alkyl, C₃-C₆-alkenyl, C₁-C₆-alkylsulfonyl, C₁-C₆-alkylcarbonyl,C₁-C₄-(alkylthio)carbonyloxy, phenylsulfonyl or phenylcarbonyl, wherethe phenyl radical of the two last-mentioned substituents may bepartially of fully halogenated and/or may carry one to three of thefollowing groups: nitro, cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl,C₁-C₄-alkoxy or C₁-C₄-haloalkoxy.
 7. A composition, comprising aherbicidally effective amount of at least one3-(heterocyclyl)-substituted benzoylpyrazole of the formula I or anagriculturally useful salt of I as claimed in claim 1 and auxiliarieswhich are customarily used for formulating crop protection agents.
 8. Amethod for controlling undesirable vegetation, characterized in that aherbicidally effective amount of at least one3-(heterocyclyl)-substituted benzoylpyrazole of the formula I or anagriculturally useful salt of I as claimed in claim 1 is allowed to acton the plants, their habitat and/or on seed.
 9. A process for preparingcompositions as claimed in claim 7, which comprises mixing aherbicidally effective amount of at least one3-(heterocyclyl)-substituted benzopyrazole or an agriculturally usefulsalt of the formula I is applied to plants, seeds and/or their habitat.10. A 3-(heterocyclyl)-substituted benzoylpyrazole of formula I asdefined in claim 1 wherein R⁷ is hydroxyl, C₁-C₆-alkoxy,C₃-C₆-alkenyloxy, C₁-C₆-alkylsulfonyloxy, C₁-C₆-alkylcarbonyloxy,C₁-C₆-alkylthiocarbonyloxy or phenylcarbonyloxy, where the phenylradical of the last-mentioned substituent may be partially or fullyhalogenated and/or may carry one to three of the following groups:nitro, cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy orC₁-C₄-haloalkoxy.
 11. A 3-(heterocyclyl)-substituted benzoylpyrazole offormula I as defined in claim 10, wherein X is O; R¹ is C₁-C₄-alkyl; R⁶is C₁-C₄-alkylthio or C₁-C₄-alkylsulfonyl.
 12. A3-(heterocyclyl)-substituted benzoylpyrazole of formula I as defined inclaim 10 wherein X is O; R¹ is C₁-C₄-alkyl; R⁶ is halogen, nitro,C₁-C₄-haloalkyl, C₁-C₄-alkoxy or C₁-C₄-haloalkoxy.
 13. A3-(heterocyclyl)-substituted benzoylpyrazole of formula I as defined inclaim 10 wherein X is N(C₁-C₆-alkyl).